Airbnb Properties for Sale in Chestertown, MD

Looking for a vacation rental investment in Chestertown, MD with high ROI ?

Explore a range of newly added short-term rental homes in Chestertown, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
119 Darden Rd CHESTERTOWN, MD Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This cha...	3 beds \| 2 baths \| 1,424 sq.ft.	$315,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 5.08% Airbnb Rental Income: $2892 Traditional Rental Income: $2055 Airbnb ROI: 5.64% Traditional ROI: 5.08%
23110 OLD FAIRLEE Road CHESTERTOWN, MD Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impress...	3 beds \| 1 baths \| 1,805 sq.ft.	$339,900	Airbnb cash on cash: 5.1% Traditional cash on cash: 3.75% Airbnb Rental Income: $2892 Traditional Rental Income: $1791 Airbnb ROI: 5.1% Traditional ROI: 3.75%
103 METCALF RD CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in this October. This home featu...	3 beds \| 2 baths \| 1,280 sq.ft.	$259,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 6.24% Airbnb Rental Income: $2892 Traditional Rental Income: $2133 Airbnb ROI: 6.6% Traditional ROI: 6.24%
22481 GOOSE HOLLOW Drive CHESTERTOWN, MD Welcome to peaceful country living with modern comfort. This beautifully updated 3-bedroom...	3 beds \| 2 baths \| 1,296 sq.ft.	$379,500	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.21% Airbnb Rental Income: $2892 Traditional Rental Income: $2156 Airbnb ROI: 4.39% Traditional ROI: 4.21%
127 Wood Duck Ln CHESTERTOWN, MD	3 beds \| 2 baths \| 1,666 sq.ft.	$215,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 6.34% Airbnb Rental Income: $2892 Traditional Rental Income: $1807 Airbnb ROI: 8.37% Traditional ROI: 6.34%
222 Dutchess Rd CHESTERTOWN, MD 222 Dutchess Rd, CHESTERTOWN, MD 21620 \| Single Family Residential	3 beds \| 1 baths \| 1,096 sq.ft.	$320,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 2.74% Airbnb Rental Income: $2892 Traditional Rental Income: $1545 Airbnb ROI: 4.99% Traditional ROI: 2.74%
Hoffecker Rd CHESTERTOWN, MD Hoffecker Rd, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$212,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 0.84% Airbnb Rental Income: $1806 Traditional Rental Income: $680 Airbnb ROI: 4.01% Traditional ROI: 0.84%

Vacation Rentals in Chestertown

There are 7 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $357,450 and the average price per square foot is $153. The cash on cash return on vacation rentals in Chestertown is 1.00%. The average monthly short term rental income in Chestertown is $1,948.

Chestertown, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 7 Airbnb properties available for sale in Chestertown.

In 2026, the best neighborhood to buy short term rental property is CHESTERTOWN.

In January 2026, the average Airbnb occupancy rate in Chestertown is 28%.

Airbnb data on vacation rentals in Chestertown, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chestertown, MD market insights, guest information and booking details, seasonality trends and historical Chestertown, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chestertown, MD

119 Darden Rd

CHESTERTOWN, MD

3 beds | 2 baths | 1,424 sq.ft.

$315,000

Airbnb cash on cash: 5.64%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $2892

Traditional Rental Income: $2055

Airbnb ROI: 5.64%

Traditional ROI: 5.08%

23110 OLD FAIRLEE Road

CHESTERTOWN, MD

3 beds | 1 baths | 1,805 sq.ft.

$339,900

Airbnb cash on cash: 5.1%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2892

Traditional Rental Income: $1791

Airbnb ROI: 5.1%

Traditional ROI: 3.75%

103 METCALF RD

CHESTERTOWN, MD

3 beds | 2 baths | 1,280 sq.ft.

$259,900

Airbnb cash on cash: 6.6%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $2892

Traditional Rental Income: $2133

Airbnb ROI: 6.6%

Traditional ROI: 6.24%

22481 GOOSE HOLLOW Drive

CHESTERTOWN, MD

3 beds | 2 baths | 1,296 sq.ft.

$379,500

Airbnb cash on cash: 4.39%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $2892

Traditional Rental Income: $2156

Airbnb ROI: 4.39%

Traditional ROI: 4.21%

127 Wood Duck Ln

CHESTERTOWN, MD

3 beds | 2 baths | 1,666 sq.ft.

$215,000

Airbnb cash on cash: 8.37%

Traditional cash on cash: 6.34%

Airbnb Rental Income: $2892

Traditional Rental Income: $1807

Airbnb ROI: 8.37%

Traditional ROI: 6.34%

222 Dutchess Rd

CHESTERTOWN, MD

3 beds | 1 baths | 1,096 sq.ft.

$320,000

Airbnb cash on cash: 4.99%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $2892

Traditional Rental Income: $1545

Airbnb ROI: 4.99%

Traditional ROI: 2.74%

Hoffecker Rd

CHESTERTOWN, MD

N/A beds | N/A baths | N/A

$212,000

Airbnb cash on cash: 4.01%

Traditional cash on cash: 0.84%

Airbnb Rental Income: $1806

Traditional Rental Income: $680

Airbnb ROI: 4.01%

Traditional ROI: 0.84%

Vacation Rentals in Chestertown

Chestertown, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

How many Airbnb properties are available for sale in Chestertown?

Which neighborhoods in Chestertown to invest in 2026 for short term rentals?

What is the average Airbnb occupancy rate in Chestertown, MD?

How to get Chestertown, MD Airbnb data?

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